of milwaukee



Patented ov. 9, P926.

l T F I JOSEPH B. OESCH, OF MILWAUKEE, WISCONSIN, ASSIGNOB T6 THE NEWPORT COM- PANY, F MILWAUKEE, WISCONSIN, A CORPORATION UT DELAWARE.

TBISAZO ZDYE AND THE PROCESS 0F ll!!!ANT)lFdtlT'tllltld.

nnoocm also 1 where the X benzene radical may be substituted by a halogenor alkyl group.

The process of manufacture consists in combining the diazotized acetylamino Cloves acid (1 acetylamino 4 naphthylamine 6 sulfonic acid, or 1 acetylamino 4 naphthylamine 7 sult'onic acid, or a mixture of both) with m-toluidine, diazotizing the intermediate dye thus obtained, combining it with m-toluidine, diazotizing the resulting disazo dyestuff, and combining the latter with salicylic acid or a substitution product thereof.

Without limiting my invention to any particular procedure, the following example in which parts by weight are given illustrates the application of my invention in the preferred form:

28 parts of acetylamino Cleves acid (1 acetylamino 4 naphthylamine 6 sulfonic acid, or 1 acetylamino d naphthylamine T sultonic acid, or a mixture of both) dissolved in 300 parts of water is cooled to 0 and acidulated with 35 parts of hydrou. ehloric acid, sp. gr. 1.163, and diazotized with 6.9 parts of sodium nitrite. The diazo compound is then added to a solution of 11.3 parts of m-toluidine and 11.6 parts of hydro chloric acid in 100 parts of water. The mixture is stirred for a short time and a solution of 25 parts of sodium acetate is slowly added and stirred until the copulation is NHCOCH some N changing with caustic ange or t I on: udw

19, 1925. Serial N0. 57,315.

molecular proportion of an end com onent .conslsting ofsahcyhc acid or 1ts su stltut1on products.

These new dyes correspond to the general 10 formula:

N=N 0 H COOH complete. The resulting amino azo dyestufit is acidulated with parts of hydrochloric acid, sp. gr. 1.163, and diazotized with 6.9 4 parts of sodium nitrite. The mixture is stirred until the nitrous acid has disappeared. The diazo compound thus obtained is added to a solution made up of 11.3 parts of m-toluidine and 11.6 parts of hydrochloric 5o acid in 100 parts of water. This is then stirred for a quarter of an hour and 25 parts of sodium acetate are slowly added. The mixture is again stirred until the copulation is complete. The amino disazo dyestud is then acidulated with 35 parts of hydrochloric acid and further diazotized with 7 parts of nitrite and the mixture stirred until diazotization is complete. The diazo compound is then added to a solution of 15.5 parts of salicylic acid, parts of Water and 106 parts of soda ash. Agitation is continued for six hours, the solution is heated and salted, filtered and dried. The new d e is, after being dried and pulverized, in t e es state of its sodium salt a dark powder easily soluble in water with an orange brown coloration and dying cotton in orange brown shades, very fast to light.

The structural formula of the specific dye to formed in the ahove example is host repre- -sented by the following:

g 1,coe,e7s

absolute alcohol, ether, or benzene. The dye OH is destroyed by strong reducing agents. 00E Ema Saucy," add The products of such reduction are probably the following: 2

NHCOCHi I am aware that numerous details of the l-acetylaminMamino-naphthaleneprocess may be varied through a wide range soaN fi'sulmmmcii (Mmm salt) without departing from the spirit of this invention, and 1 do not desire limiting the patent granted other than as necessitated by NHS the prior art,

H I claim as my invention: ggggigg methyl'p'phenylene' 1. As an article of manufacture, a trisazo dye as herein described, having most probn, ably the following formula:

NHCOCHs N=N a SOzNa..-

N=N N=N wherein the hydrogen atoms in X, y and z positions in the X benzene radical may be substituted by a halogen or an alkyl group, this dye being in the shape of its sodium salt a dark powder soluble in water to anorange-brown solution, the color of the 501111., tion changing with caustic soda to redbrown; with hydro-chloric acid the dye be ing separated out as a brown flocculent precipitate; said powder being insoluble in organic solvents such as absolute alcohol, ether and benzene, being destroyed by strong reducing agents and the dyeings on cotton being orange to brown.

2. As a new article of manufacture a trisazo dye as herein described having most probably the following formula:

3. The method of preparing a trisazo dye of the general formula:

NHCOCH];

which consists in combining acetylamino Cloves acid with m-toluidine, diazotizing the intermediate compound thus obtained, combining it with m toluidine, diazotizing the disazo compound, and combining the last mentioned compound 'with salicylic acid 4. Materials dyed with the dye prepared,

40 according to claim 1.,

Josnrn B. oases.

dye prepared, 

